Organosilicone compounds having alkynol groups and the use thereof in crosslinkable materials

Abstract

Organosilicon compounds having alkynol groups and containing units of the formula where R 3 and R 2 are optionally substituted hydrocarbon radicals, R 4 are divalent organic radicals, and X is a linking group are useful in addition crosslinkable compositions. The compositions exhibit long pot life and yet also exhibit excellent cure, and are useful, inter alia, in preparing molded articles and coatings.

1. An organosilicon compound having alkynol groups and comprising units of the formula 
       
         
           
           
               
               
           
         
       
       in which
 R 2  are identical or different and are a hydrogen atom, a radical —OR 5 , or an optionally substituted hydrocarbon radical, 
 R 3  are identical or different and are a hydrogen atom, a halogen atom, a radical —OR 5 , or a monovalent, optionally substituted hydrocarbon radical, 
 R 4  are identical or different and are a divalent organic radical, 
 X are identical or different and are —O—, —S—, —OC(═O)—, —N(R 6 )— or —N(R 6 )—C(═O)—, 
 R 5  are identical or different and are a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical, 
 R 6  are identical or different and are a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical, 
 e is 0, 1, 2 or 3, 
 f is 0, 1, 2 or 3, 
 g is 0 or a positive integer and 
 h is 0 or a positive integer, 
 
       with the proviso that the sum e+f is less than or equal to 3 and the organosilicon compound has at least one unit of the formula (III) where e is not zero. 
     
     
       2. The organosilicon compound of  claim 1 , wherein X is —O—. 
     
     
       3. The organosilicon compound of  claim 1 , wherein the sum e+f<3. 
     
     
       4. The organosilicon compound of  claim 2 , wherein the sum e+f<3. 
     
     
       5. A crosslinkable material comprising
 (A) one or more compounds which contain radicals having aliphatic carbon-carbon multiple bonds, 
 (B) at least one organosilicon compound having Si-bonded hydrogen atoms, 
 (C) at least one organosilicon compound of  claim 1  having alkynol groups and containing units of the formula (III), 
 
       
         
           
           
               
               
           
         
       
       in which
 R 2  are identical or different and are a hydrogen atom, a radical —OR 5 , or an optionally substituted hydrocarbon radical, 
 R 3  are identical or different and are a hydrogen atom, a halogen atom, a radical —OR 5 , or a monovalent, optionally substituted hydrocarbon radical, 
 R 4  are identical or different and are a divalent organic radical, 
 X are identical or different and are —O—, —S—, —OC(═O)—, —N(R 6 )— or —N(R 6 )—C(═O)—, 
 R 5  are identical or different and are a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical, 
 R 6  are identical or different and are a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical, 
 e is 0, 1, 2 or 3, 
 f is 0, 1, 2 or 3, 
 g is 0 or a positive integer and 
 h is 0 or a positive integer, 
 
       with the proviso that the sum e+f is less than or equal to 4 and the organosilicon compound has at least one unit of the formula (III) where e is not zero, and
 (D) at least one catalyst which promotes the addition of Si-bonded hydrogen at an aliphatic multiple bond. 
 
     
     
       6. The crosslinkable material of  claim 5 , wherein at least one component (A) comprises an aliphatically unsaturated organosilicon compound. 
     
     
       7. The crosslinkable material of  claim 5 , wherein component (C) is present in an amount of from 0.0001 to 70% by weight, based on the weight of component (A). 
     
     
       8. The crosslinkable material of  claim 5 , comprising:
 (A) at least one compound which contain radicals having aliphatic carbon-carbon multiple bonds, 
 (B) at least one organopolysiloxane having Si-bonded hydrogen atoms, 
 (C) at least one organopolysiloxane having alkynol groups and containing units of the formula (III) where the sum of e+f≦3, 
 (D) at least one catalyst which promotes the addition of Si-bonded hydrogen and an aliphatic multiple bond, and optionally, 
 (E) reinforcing fillers. 
 
     
     
       9. The crosslinkable material of  claim 5 , comprising:
 (A) substantially linear compound(s) which have on average at least two radicals having aliphatic carbon-carbon multiple bonds, 
 (B) organopolysiloxanes having on average at least two Si-bonded hydrogen atoms, 
 (C) organopolysiloxanes having alkynol groups and containing units of the formula (III), 
 (D) at least one catalyst which promotes the addition of Si-bonded hydrogen at an aliphatic multiple bond, 
 (E) optionally reinforcing fillers, 
 (F) optionally further components, and 
 (G) optionally inhibitors and/or stabilizers. 
 
     
     
       10. The crosslinkable material of  claim 5 , wherein the sum of e+f is less than or equal to 3. 
     
     
       11. A process for producing a molding, comprising adding to a mold a crosslinkable material comprising:
 (A) one or more compounds which contain radicals having aliphatic carbon-carbon multiple bonds, 
 (B) at least one organosilicon compound having Si-bonded hydrogen atoms, 
 (C) at least one organosilicon compound of  claim 1  having alkynol groups and containing units of the formula (III), 
 
       
         
           
           
               
               
           
         
       
       in which
 R 2  are identical or different and are a hydrogen atom, a radical —OR 5 , or an optionally substituted hydrocarbon radical, 
 R 3  are identical or different and are a hydrogen atom, a halogen atom, a radical —OR 5 , or a monovalent, optionally substituted hydrocarbon radical, 
 R 4  are identical or different and are a divalent organic radical, 
 X are identical or different and are —O—, —S—, —OC(═O)—, —N(R 6 )— or —N(R 6 )—C(═O)—, 
 R 5  are identical or different and are a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical, 
 R 6  are identical or different and are a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical, 
 e is 0, 1, 2 or 3, 
 f is 0, 1, 2 or 3, 
 g is 0 or a positive integer and 
 h is 0 or a positive integer, 
 
       with the proviso that the sum e+f is less than or equal to 4 and the organosilicon compound has at least one unit of the formula (III) where e is not zero, and
 (D) at least one catalyst which promotes the addition of Si-bonded hydrogen at an aliphatic multiple bond, 
 
       and crosslinking said crosslinkable composition. 
     
     
       12. The process of  claim 11 , wherein at least one component (A) comprises an aliphatically unsaturated organosilicon compound. 
     
     
       13. The process of  claim 11 , wherein component (C) is present in an amount of from 0.0001 to 70% by weight, based on the weight of component (A). 
     
     
       14. The process of  claim 11 , comprising:
 (A) at least one compound which contain radicals having aliphatic carbon-carbon multiple bonds, 
 (B) at least one organopolysiloxane having Si-bonded hydrogen atoms, 
 (C) at least one organopolysiloxane having alkynol groups and containing units of the formula (III) where the sum of e+f≦3, 
 (D) at least one catalyst which promotes the addition of Si-bonded hydrogen and an aliphatic multiple bond, and optionally, 
 (E) reinforcing fillers. 
 
     
     
       15. The process of  claim 11 , comprising:
 (A) substantially linear compound(s) which have on average at least two radicals having aliphatic carbon-carbon multiple bonds, 
 (B) organopolysiloxanes having on average at least two Si-bonded hydrogen atoms, 
 (C) organopolysiloxanes having alkynol groups and containing units of the formula (III), 
 (D) at least one catalyst which promotes the addition of Si-bonded hydrogen at an aliphatic multiple bond, 
 (E) optionally reinforcing fillers, 
 (F) optionally further components, and 
 (G) optionally inhibitors and/or stabilizers. 
 
     
     
       16. The process of  claim 11 , wherein component (C) is present in an amount of 0.02 weight percent to about 10 weight percent, based on the weight of component (A).